Yes You Would Have To Restain It every year or so if it is bleached out if you just got it you should what tell you restain it for a couple of months
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Teak, or cedar
You need to tell us what wood you are staining ! -All woods respond differently to different stains.
You can stain balsa wood.
I agree with Charles. I would also sand the piece of wood with the stain a bit then apply the darker stain.
Wood stain is abosorbed into the wood, so the wood takes on the color of the stain. This is why the features of the wood are still visible, unlike with paint.